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In 2026, a full tear-off and replacement on Long Island runs about $530–795 per square (100 sq ft) for architectural asphalt, $900–1,620 for cedar, $1,050–1,785 for standing seam metal and $1,155–1,890 for synthetic slate; natural slate is $2,000–3,500 per square nationally. A typical 2,500–4,000 sq ft East Hampton roof is 25–40 squares, so asphalt lands around $13,250–31,800 and cedar or metal well above that. East Hampton jobs tend to sit at the top of the ranges because of access, roof complexity and material grade.

Plan on 20–40 years. The Cedar Shake & Shingle Bureau puts the average at 30–40 years and a well-maintained roof at up to 50. In the Hamptons the spread is driven by exposure and maintenance: a shaded Northwest Woods roof that is cleaned every 3–5 years and re-treated every 5–7 can reach the long end; an oceanfront roof in Montauk or Sagaponack that never sees a brush will sit at the short end, and its flashing, fasteners and gutters will usually fail before the wood does.

Usually yes for a tear-off. Across Suffolk County the pattern is that a replacement that goes down to the sheathing needs a building permit, while a shingle-over-shingle recover often does not. In the Village of East Hampton permits typically take 2–4 weeks when the application is complete; the Town of East Hampton (Springs, Wainscott, Amagansett, Montauk, Northwest) has reported a backlog of 16–20 weeks against a statutory 15-day clock. In the village's four historic districts, a visible change of roof material also needs a Certificate of Appropriateness; a new wood-shingle roof is exempt. Confirm with the building department before ordering material.

The work itself is quick: asphalt 1–3 days (one day for a simple roof, two or three for a complex one), cedar 3–6 days, slate 6–10 days, plus weather. The calendar is dominated by what comes before: a permit (2–4 weeks in the Village of East Hampton; a reported 16–20 week backlog in the Town of East Hampton; the Town of Southampton is generally faster), design review in the villages' historic districts, and material lead time, which is longest for cedar, slate and copper. Book a spring roof in winter.

There is no single answer, but there is a short list. Standing seam in aluminum or copper handles wind best and shrugs off salt (40–70+ years for aluminum, 70–100+ for copper). Natural slate lasts 75–200 years and resists wind once properly hung, with copper fasteners. Cedar is the traditional choice and works if it is fastened for wind and maintained on schedule, at the short end of its 20–40 years. Architectural and designer asphalt is the budget option, with some designer lines wind-rated to 130 mph. Whatever the covering, the details decide it: full ice-and-water shield, stainless or copper metal.

It costs homeowners nothing. You tell us about the job once, roughly sixty seconds, where the house is, what is going on, and when you want it handled. We match you with one licensed, insured roofer who works your town and is right for the material and the job, and they call you within one business day to look at the roof and quote it directly. We are a Hamptons-only referral service, not a roofing contractor and not a marketplace: one roofer, not a bidding pool, and nobody else gets your number. Participating roofers pay us a referral fee.